Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes

Authors
Marko, IE Murphy, F Kumps, L Ates, A Touillaux, R Craig, D Carballares, S Dolan, S
Citation
Ie. Marko et al., Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes, TETRAHEDRON, 57(13), 2001, pp. 2609-2619
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
13
Year of publication
2001
Pages
2609 - 2619
Database
ISI
SICI code
0040-4020(20010326)57:13<2609:EPOTAU>2.0.ZU;2-O
Abstract
High yields of di- and tri-substituted alkenes are: obtained by a modificat ion of the Julia-Lythgoe olefination reaction involving the in situ capture of intermediate beta -alkoxy-sulfones by benzoyl or trimethylsilyl chlorid e, followed by SmI2-mediated reductive elimination. This novel protocol als o provides a connective preparation of dienyl ethers, which are important p artners in Diels-Alder cycloadditions. (C) 2001 Elsevier Science Ltd. All r ights reserved.